


Take A Memo, Miss Ackles

by dastiel_gal (rock_chick)



Series: Secretary [2]
Category: Supernatural RPF
Genre: Alternate Universe - Gender Changes, F/M, Trans Female Character
Language: English
Status: Completed
Published: 2010-10-11
Updated: 2010-10-11
Packaged: 2017-10-24 06:50:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,040
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/260345
Author URL: https://archiveofourown.org/users/rock_chick/pseuds/dastiel_gal
Summary: <blockquote class="userstuff">
              <p>Jeff and Jared are busy re-enacting <i>Secretary</i> in the office with Jenny, their gorgeous assistant, when they make a surprising discovery about her.  They run with it.  (Pre-op trans Jensen)</p>
            </blockquote>





	Take A Memo, Miss Ackles

**Author's Note:**

> Written for [](http://triceybabe.livejournal.com/profile)[**triceybabe**](http://triceybabe.livejournal.com/) as part of the [SPN Threesome Exchange](http://community.livejournal.com/spnthreesome/). I read the assignment and said, "Hang on, I think I already wrote this fic... sort of." A few months ago, I wrote J3 cross-dressing kink for [](http://blindfold-spn.livejournal.com/profile)[**blindfold_spn**](http://blindfold-spn.livejournal.com/). It was wildly cracky, and although there was a short sex scene in there, I wasn't feeling the porn that day, so I concentrated on the kink rather than the sex. However, the scenario fit [](http://triceybabe.livejournal.com/profile)[**triceybabe**](http://triceybabe.livejournal.com/)'s prompts so well that I decided to write a vastly extended version of the skimmed-over sex from that fic, minus the crack and from a different POV. This can be read as stand-alone porn, or if you want the backstory, read [James Spader, Eat Your Heart Out](http://dastiel-gal.livejournal.com/13736.html) first. Many thanks to [](http://salmon-man.livejournal.com/profile)[**salmon_man**](http://salmon-man.livejournal.com/) for checking this over for me and cheerleading!

"What do you mean, she's not a she?" Jared stares at his boss, his face a picture of confusion and outright shock. He feels like someone just chucked a bucket of icewater over him, and his dick, which has been diamond-hard for the last half hour, is softening rapidly. This whole situation has been borderline out of control ever since they came out of a late meeting and Jeff decided to take advantage of the dark emptiness of their workplace to re-enact scenes from _Secretary_ on their assistant, Jenny, and it just tipped all the way over into Too Fucking Much To Handle.

Jeff is biting his lip, staring at Jenny, and Jared can't tell if it's because he's uncomfortable, or if the bastard is trying not to laugh. "I mean, she has a penis. He has a penis. I just copped a feel, and there it was."

That's ... just crazy. They have the hottest secretary in the entire company. She has soft pouty lips and long shapely legs! Jared has been jerking off to fantasies of her for _weeks_. She's not a guy. She can't be! Jared looks down to Jenny, still lying where he's been holding her bent, skirtless, across the desk while Jeff spanked her. Her wrists feel so small in his hands, of course it isn't true... but then he realizes that Jenny is blushing like fire, all over her head, ears and neck, and is trying to bury her face in her shoulder. The mortification is coming off her - him? - her in waves. Oh, God. It _is_ true.

"Don't worry about it, sweetheart," Jeff says, beaming down at her. "I swing both ways."

He _does??_ Jared leaves off gawping at Jenny, and gawps at Jeff instead. He's starting to think he's fallen down a rabbit-hole and got stuck in the freakiest dream he's ever had. His hands slip off Jenny's wrists and he slumps dizzily into Jeff's chair. He sits there, trying to think this through and going nowhere fast; he doesn't know what the hell he's feeling, or even what he _should_ be feeling. Can barely sort out which way is up. His sex life so far has been pretty ordinary and entirely satisfying, but now everything is turned on its head and up in the air and... Christ, he doesn't know what the fuck is going on. He watches, bemused, as Jeff pulls a trembling Jenny gently off the desk and tucks her into his arms, whispering reassurance and endearments into her ear.

"You okay there, Padalecki?" Jeff's bass rumble interrupts his abstractions.

"I just... this is... um."

"Chill, man. She's still our Jenny. We _like_ her. Don't we?" Jeff's eyes pin him down, daring him to deny it at his peril.

"Well, yeah, of course, I just... I..."

"Well, then. Nothing to get aerated about, right?" Jeff uses his knuckles to tip Jenny's chin up, waits till she raises her eyes to his. "We're okay, darlin'. Ready to carry on?"

Jenny nods her agreement, and Jeff's gaze swings to Jared. "How about it, lad? You still in?"

Jared stares at him, open-mouthed. "But... You're still gonna...?"

Jeff shrugs at him, grinning, then saunters out to the secretary station. Jared looks at Jenny, who has not stopped blushing furiously and can't meet his eye.

"I'm sorry, Jared," she whispers, barely audible. "I wanted to tell you, I just... I didn't know how, and I didn't expect this..." Her voice wobbles into silence, and Jared isn't asshole enough to want to see her cry. He stands and walks around the desk, puts a comforting hand on her arm.

"It's okay, Jenny. Really. It's just... a lot for me to take in."

Jeff comes back with Jenny's wheelie chair and indicates to Jenny that she should sit in it. She complies demurely, crossing her knees, and her movements draw Jared's eyes to her flawless legs, encased in black nylon. The legs that have been driving him crazy with want, every time she wears a short skirt. Jared's eyes sweep upwards of their own accord, to the lace at the top of the hold-ups and the creamy skin above that. His cock twitches, against his better judgement.

Jeff chuckles, well aware of the direction of Jared's gaze and seemingly able to see right into Jared's head. "Lovely, ain't she?"

He swings the chair around so Jenny has her back to them, orders her to put her arms behind her - Jared hears her gasp at the demanding tone of Jeff's voice - and then uses his tie to lash her wrists to the back of the chair, and that's just... Jared doesn't know _what_ it is. There's a pounding in his ears and his head is spinning. He realizes belatedly that he isn't breathing, drags air into his lungs and nearly chokes on it.

Jared stares slack-jawed at Jenny's wrists crossed and bound to the chair, which is absolutely the hottest thing he has ever seen. He'd thought the spanking was so wild, Jeff's hand cracking against Jenny's lace-clad ass, desperate little gasps and cries escaping her, but this is way beyond. Jared's higher brain function is shutting down, his blood all diverted southwards. He wonders what she'd look like tied up with rope, or in handcuffs. _God._ That would be amazing. His cock throbs, all the way hard again now and tenting his pants.

Jeff spins Jenny back round, and wheels her up to Jared slowly, giving him time to look his fill. "Open wide, Jenny." He looks at Jared, who gapes back speechlessly. "Jared, man, what are you waiting for? Pants unzipped. Blowjob."

Jared doesn't think he could find his voice if his life depended on it. He looks down into Jenny's eyes, which are dark and shining with desire, then further down to her soft, glossy mouth. Her lips part invitingly, and Jared rushes to undo his zipper, hands clumsy as he tries to get himself out as quickly as he can.

Jenny peeps up at him through her lashes as her tongue flicks over him, teasingly, then she leans forward and takes the head into her mouth, closing around it, sucking hot and wet, and Christ, that feels heavenly. She pulls off again, leaving a ring of red gloss around him, which is a huge turn-on that Jared didn't even know he had, and he moans, needy and wanting more. She goes to take him back in and misses, his cock sliding up the outside of her face, leaving a wet trail of precome on her cheekbone. She chases it, but tethered as she is, she can't get the right angle; it keeps sliding away from her.

Jared bites off a desperate snarl, grabs the base of his cock with one hand and Jenny's chin with the other, gets them lined up and feeds it to her, pushing in all the way until the edge of his fist meets her lips. She moans around him, writhing against her tied hands, and he shudders, fighting the urge to cut loose and fuck her mouth roughly. He pulls out, her lips dragging all the way up and leaving more smears of red gloss on him, then back in as far as she can take him.

"He's got a lovely big cock, hasn't he, sweetheart?" rumbles Jeff, rubbing lazily at his own through his pants. "Makin' me so horny, watching you suck him. Can you take it harder?"

Jenny nods as best she can as Jared pulls out, hums her agreement around his head. Jared whines, pushes in again fast and sets up a punishing rhythm that makes her gag on the first couple of thrusts until Jeff steadies her with his hands on her shoulders and she relaxes and opens up around him. It's the hottest, filthiest blowjob Jared has ever had, and his whole body is lighting up from the inside out. He wants it to last forever, knows it can't, feels his climax build in his balls and heat start to roll out through his body.

"Gonna," he gasps, barely coherent, " _now_ ," thrusts in for the last time and shoots down her throat, grunting and shuddering as she coughs around him and tries to swallow. As he comes down, he realizes her eyes are watering, tears and streaks of make-up running down her face, and a wave of guilt hits him. Oh, God, he hurt her! He falls to his knees in front of her, babbling apologies until she shuts him up by kissing him.

"It was really hot," she says, pink-cheeked and breathless, the same swoony expression in her eyes as she had when they were spanking her, and Christ, maybe she really does like it rough. He peppers kisses over her face, wiping the smeared makeup away as best he can.

"Such a good girl," smiles Jeff, loosing her hands and massaging her wrists, "blowing Jared so nice. He's been wanting you ever since he laid eyes on you, and so have I."

Jared hauls himself up and staggers back to lean on Jeff's desk. He watches as Jeff stands Jenny up, snuggles against her back and starts nibbling at her neck, running his hands over her body until she moans and wriggles against him. He's gentle but sure, stroking and squeezing, driving her wild with it. He takes his time, popping the buttons on her shirt one by one, slowly exposing the silvery-grey satin corset she's wearing underneath. It looks so sexy, the way it nips in at her waist and flares out again over the hips. Jeff slips off her shirt and puts his big hands around her middle, his fingers nearly meeting, and Lord, that looks so good Jared can feel it _everywhere_.

He's so busy dealing with the wave of desire rolling through him that he barely notices that the top of the corset is padded out over an undeniably flat male chest, and by the time his gaze sweeps downwards to the thick hard cock straining at the front of the lacy knickers, he's halfway past caring. Especially when Jeff's hand slides down to cup Jenny and she bucks up into his hand, groaning. Jared can see the cockhead poking up out of the top of the lace, and he unconsciously licks his lips.

What's left of his brain is trying to ask why the hell he's still here, and not running for the hills - he just got a blowjob from a cross-dressing _dude_ , for Chrissakes, shouldn't he be freaking out about that? - but the question seems vague, unimportant; he doesn't feel like he wants to run for the hills. What he wants is to stay right here and fuck Jenny. There's nothing vague about _that_ thought, and it fetches him up off the desk, gasping in shock.

"In the land of the living again, lad?" mocks Jeff, grinning. "We need condoms, and something to use for lube." Jenny mumbles something into Jeff's neck, blushing again, and he bellows a laugh. "In Jenny's purse. What a naughty girl you are!"

Jared fetches the purse, getting back into the office just in time to see Jeff bending Jenny over his desk for the second time that night and slipping the knickers off her pert ass. He's so distracted by the sight of black lace slithering down her legs to sit around her ankles, just above the wicked spike heels, that he barely notices her reaching over and taking her bag from him, rummaging in it and handing a small bottle to Jeff. He's starting to think he may have a tiny little lingerie fetish, or maybe it's just a Jenny-in-lingerie fetish.

He gets back with the programme when he hears Jenny moan loudly. His eyes fly back upwards to see Jeff's slick fingers working slowly between Jenny's cheeks, teasing her _again_ , and she's wriggling and biting her lip with need. As he watches, Jeff slips a finger in, making her shudder and gasp. He works it a little, then adds another and fingers her gently for a couple of minutes until she starts pushing her hips back to meet him. "More?" Jenny nods, sticking her ass out in slutty supplication, and he adds a little more lube and a third finger.

"You ready again, Jared?" Jeff asks him, and God, he is, so very ready.

"Hell, yeah, but... don't you want to?"

"Nah, man, after watching her suck you, I need that mouth on me. You're gonna fuck her."

Jeff flips him a condom, then leads Jenny round behind his desk and sprawls into his big chair, swinging it sideways to face her. He grunts contentedly as she bends over to unzip him, then draws his cock out and strokes it. She stands straight-legged, pushing her butt out pin-up style and wiggling it enticingly; looks over at Jared, flutters her eyelashes up at him and breathes, "Please, Jared, I want you." He doesn't hesitate. He rolls the condom on in a second, strides around the desk, grabs hold of Jenny's hips as she leans over Jeff's lap, and pushes the head of his cock straight in just as she takes Jeff's cock in her mouth. She squeals around her mouthful, the vibration making Jeff jerk and groan. Jared works himself in and out of her, going a little deeper every time. He's glad he's already come once, so he has the control to take it slow; he's big and he doesn't want to hurt her. She feels so fucking wonderful around him, hot and slick and tighter than anything he's ever known before, and God, if he'd known anal sex felt this good, maybe he wouldn't have always been so vanilla.

Jared speeds up a little, pushing her harder down onto Jeff, and she clings to the arms of the chair and lets him set the rhythm with his hands on her hips, pulling her back onto his cock and then pushing her off and forward to take Jeff in deep. She's moaning continuously around Jeff, who's been hard forever by now and is red in the face and groaning, pumping his hips up to meet her mouth. He's gritting his teeth, trying not to come, but Jared knows what that beautiful mouth feels like so he doesn't rate Jeff's chances of holding off. Sure enough, he only lasts a couple of minutes before he comes, bucking wildly and growling.

Jenny swallows every drop Jeff gives her, suckles him clean as best she can, but as he goes soft she lets him fall, pushes herself up on straight arms and braces herself for Jared. It's a much better angle for her, and Jared's first thrust makes her cry out and shudder against him. "God, just like that... _Jared._ "

Jared's overwhelmed by a sudden wave of nameless emotion, wants so badly to make her scream and come apart in his arms. Keeping up his rhythm inside her, he slides one hand round from her hip, strokes over her belly and down into her curls. He runs his fingers through them for a moment, before dipping around and down to caress her balls, rolls them gently in his fingers the way he likes it when he's jerking off. Jenny moans loudly, writhing wantonly against his hips.

Jared's so intent on making her feel good, it doesn't even occur to him that this is the first junk he's ever touched apart from his own. It doesn't feel the least bit weird to be pleasuring Jenny, and his hand slides up without hesitation to close around her hard, weeping cock. He pulls at her firm and fast, using her precome to slick his way, his cock pumping into her like a piston. She's making so much noise now, biting out swear-words he's never heard from her before as his every thrust sends waves of heat and need through her, and it's so hot that Jared has to bite his lip sharply to distract himself. He wants her to come first, on his cock, trapped between his hips and his hand.

She's teetering on the edge, shaking and babbling Jared's name. She clutches at Jeff's shoulders to hold herself steady, and he grabs her chin, kisses her hard and growls, "Come on, sweetheart, Jenny, come for us," and she's _there_ , writhing and bucking against them with loud cries of ecstasy. She clamps down tight on Jared, pulling him over the brink with her, and he hollers and bites down on her shoulder, still pumping his hips as he comes inside her.

Jenny's legs give out and she collapses forward into Jeff, dragging Jared with her. He slips out and falls to his knees, slumping untidily over them with his arm still around her waist, and they lie there in a heap for a few minutes, gasping and trembling. Jared starts giggling weakly, exhausted and boneless and completely unable to process the events of this evening.

Jeff looks a touch concerned. "You okay there, son?"

Jared shakes his head, not meaning _no_ , shrugs in befuddlement, and keeps twitching out giggles until Jenny slithers down into his lap and kisses some sense back into him. "Er. Um. Yeah, I'm okay. I think."

"Oh, good. I think she killed me." Jenny blushes around a huge grin, and peeps up flirtatiously at Jeff as he fixes her with a stern look, then continues, in a mock-pompous voice, "Well, Miss Ackles, I'm very pleased to announce that you have passed your first performance review with flying colours. However, Kripke & Gamble is a well-respected firm with very high standards, and you should constantly strive to give satisfaction to your immediate colleagues. I intend to be most exacting in this regard."

Jenny can hardly contain her laughter, and Jared doesn't even try. Jeff grins. "Eh, get yourselves off home and get some sleep. We've got that big report to finalize tomorrow."

They get their clothing back to rights, pack up for the night, and head down in the elevator. As the doors open onto the lobby, Jeff steps out first, looks back over his shoulder and drawls, "Leave your panties at home tomorrow, Miss Ackles. You too, Padalecki," and then strides nonchalantly off, leaving them to stare open-mouthed after him.


End file.
